


Assistance Required [Working Title]

by PatchouliRolling, shadytay



Series: Sugar Babes AU [1]
Category: Undertale (Video Game)
Genre: Alternate Universe - Underfell (Undertale), Body Dysphoria, F/M, Female descriptions may be used during sex scenes, Gang AU, Gender Dysphoria, M/M, NO FONTCEST, Other, Other Additional Tags to Be Added, Pre-Testosterone, Pre-Transtion, Pretty much Boss and Red are sugar daddies, Self-Indulgent, Self-Insert, Smoking, Sugar Daddy, Underfell Papyrus (Undertale), Underfell Sans (Undertale), attempted slow burn, but they wind up falling for us, i'm not very good with tags, soul bonding
Language: English
Status: In-Progress
Published: 2018-10-10
Updated: 2018-10-10
Packaged: 2019-07-29 00:03:02
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,683
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16252514
Author URL: https://archiveofourown.org/users/PatchouliRolling/pseuds/PatchouliRolling, https://archiveofourown.org/users/shadytay/pseuds/shadytay
Summary: Two down on their luck humans cross paths with the most notorious monster gang in the entire city.My half of the Sugar Babes AU! My part will focus on my relationship with Papyrus whilePatchouliRolling's is with her and Sans.There will be some overlap between the two but they are both separate stories, so please read both!





	Assistance Required [Working Title]

Mason never thought he would be in this situation, stuck in the middle of a bank robbery being committed by a monster gang. And not just any monster gang, the original monster gang led by the "Great and Terrible" Papyrus. Mason stood there in shock for a few moments before complying to the shouts of "get down on the ground!" being spewed out of one monster's mouth. A few shots went off, making Mason quake in fear. There was no way, he was going to live. These guys killed people for fun. Well, at least that’s what he read of the internet

"Okay boys, calm down. Sorry for the commotion everyone." Mason looked up, hoping that this was all just a silly, but horrible prank. However all he could see a tall skeleton monster walk in, adjusting one of his leather gloves. From the descriptions posted all over the media, that must be Papyrus. 

"We are only here for your money. And maybe a hostage or two." Papyrus looked straight at Mason with a smile before ordering his underlings about to different tasks. Mason's hands were tied and was being escorted to a van along with another person who happened to be at the wrong place at the wrong time. Moments later, they were both blindfolded. This was it. They were definitely going to kill him. He didn’t have anyone that cared about him, what kind of use would he even be to a gang or monsters? 

"that it boss?" Mason heard from the driver’s seat.

"Yes, now let's get home." He felt the van roar to life underneath him as the monsters made their getaway. It felt like forever, even with his heart racing, for them to get where they were going. And it was even longer before Mason and the other person was pulled out of the back. Mason walked for a while, being led down hallways and stairs, god, so many stairs. Before being sat down in a chair and secured to it. His blindfold was then removed to see Papyrus crouching to be face to face with him. They were in a dark and rather musty room. Mason’s eyes immediately started to tear up. This was it, time to beg for mercy.

"Tell me about yourself." Papyrus said firmly.

"Please don't hurt-" He put a finger up to Mason's lips.

"I said tell me about yourself, not beg. Or if you rather, I'll give you something to beg about." He stood up and went to lean against a table, crossing his arms. "Now go on."

Mason took a deep breath, trying to steady himself. But the wavering in his voice was still apparent. "I was kicked out of my house a few years ago by my parents when I came out. I lived on the streets for a while, working odd jobs until I could afford rent. Things haven't been good for me lately because I've been on unemployment and that's why I was at the bank, cashing a check."

"What did you come out as?"

"Nonbinary and transgender. I haven't been able to afford any treatment or even a binder but it's not a big deal. I mean, you are going to kill my anyways right? My parents don't want me, so you can't hold me for ransom."

Papyrus thought for a moment. "I have a better idea." He walked back over to Mason. "I have a proposition for you. Choose not to accept, and you can return to your high life of cashing unemployment checks and barely making rent. Or, you can become my, let's say assistant. I'll give you money for what you need, and you'll help me out with a few, more personal needs. So what do you say?"

Immediately Mason knew his answer, "I'll gladly be your assistant!"

"Good, you start now. Let's get you untied."

Soon Mason was walking upstairs, being led by "Boss". As Papyrus has instructed Mason to call him. He look a look around on the walls, a few paintings here, a photo there of the gang members on vacation.

"Everyone." Boss announced to the crew sitting in the living room, counting up the cash. "Meet Mason. He will be my assistant from now on. And only MY assistant, you hear that?" There were a few nods around the room and several "yes, sirs" being passed around.

"Good. Now I'm going to show him the ropes." Boss led Mason about the mansion, explaining how everyone in the crew lived here and they were a family. Everyone is important.

"Now if one of those assholes touch you, or bosses you around, tell them to fuck off. Then tell me and I'll take care of it." He said before opening a door. "Now, this will be your room." The room was pretty bare, a twin sized bed, a small desk, and a dresser.

"I know it's not very decorated, but think of it as a blank canvas. We will go shopping for decorations and such later. I'll also have some of my boys pick up your stuff from your apartment." Boss took a step back and examined Mason's clothing. "However, we will have to redo your wardrobe. I am a skeleton with standards and your current style of clothing is not up to par." He tapped his chin. "I suppose I do have a few spare shirts lying around that may fit a larger gentleman like yourself. If need be, I can steal a few of my brother's. Stay here." Mason was left alone in his room, finally a moment to himself. He sat down on the bed and found that his phone was still in his pocket. He opened it to find messages from his roommate.

xxx-xxxx 4:30 pm  
Hey the bank is gonna close soon. You should go so you can cash that check.

Mason 4:31 pm  
Already out the door

xxx-xxxx 5:42 pm  
If you are at the store, pick up some paper towels and eggs

xxx-xxxx 7:05 pm  
Where the fuck are you? You said you didn't have any plans.

Mason sighed, he should probably call them so they wouldn't worry. He clicked the call button and waited for his roommate to pick up.

"Dude, where the fuck have you been? You never go out for more than an hour or two without telling me."

"Sorry I got into a... situation. I don't think I can tell you much right now, but I am moving out."

"What?" Mason put a hand on his head, trying not to freak his friend out.

"Just, there are going to be some monsters coming over to pick up my stuff. Try not to freak out too much and help them pack please. I'll love you forever." 

He heard a sigh from over the line. "Alright, alright. But you gotta pay for the rest of this month's rent too." Mason agreed and said his goodbyes right before Boss came back in with with a few hangers of clothes. He laid them down on the bed beside Mason then went to lean against the dresser.

"Go on try them on."

Mason blushed a bit. "In front of you?" 

"Yes."

He took a deep breath and looked through his options. Several dark button ups, some dress pants... A skirt? Mason held it up with a confused look on his face. Boss looked away but Mason could see a small blush creep across his cheek bones. 

"I didn't know what kind of clothing you would be into, you know. They are all just pieces of fabric in the end."

Mason smiled. It was a pretty cute skirt, and it had some shorts built in to it. Nice.  
He started undressing, back to Boss to have some sense of privacy. He took off his shirt and looked down at his chest. It was being flattened by a sports bra that was a size too small. A wave of discomfort fell over him as he tore his eyes away and put on the maroon button up and a pair of grey dress pants. He turned back around to Boss.

Boss thought for a moment before coming over and loosely tucking in the shirt and helping roll up the sleeves.

"Much better." 

\---

Rules:  
1\. Stick with Boss while he is at home.  
2\. Help prepare meals with the crew members. (this is the ONLY thing you should help the crew with)  
3\. If you need money, just ask.  
4\. Be prepared for anything.

\---

Mason found himself waking in Boss's bed, the skeleton's legs tangled with his. Mason thought back onto last night.

"I know I briefly introduced Mason as my assistant post heist, but I believe it is time to get on with proper introductions." They were standing in front of the whole crew, a set of about fifteen monsters, in the large living room. Boss gave a pat to Mason's back, gesturing him to make an introduction.

"Um, Hi." He waved, a bit intimidated by all the monsters staring at him. "My name is Mason, I'm 20 years old."

"Way to go Boss!" One of the monster's shouted before the skeleton shot him a glare.

"Uhh, I use he him pronouns. I'm okay with they them too." 

A few monsters nodded, a few others looked a bit confused. Boss stepped back in front of Mason, taking control of the meeting. 

"Mason is to help me in a few personal requests, and to help you heathens cook. That's all you can ask him to help with. Speaking of, what are we having tonight?" 

The human smiled wide, "Chicken fettuccine alfredo! Since there are so many mouths to fed, I am going to need some help." A few hands shot up and Boss chose the ones he could trust to keep their hands to themselves. 

Mason found himself commanding the kitchen, two members were preparing the chicken, another was keeping an eye on the pots, waiting for them to boil. Mason was in the pantry, gathering ingredients for a dessert. When he came out he found a shorter, chubby skeleton sitting at the counter.

"i don't know what boss sees in ya kid. normally he goes after hot sexy ladies. not squishy trans people." 

"Ah, you must be Red." Mason remembered what Boss said about getting pushed around. "Would you kindly fuck off? I have food to make. And maybe if you ask real nice, I'll give you an extra helping of ligma."

"the fucks ligma?"

"Ligma balls bitch."

Red gave a hearty laugh, a genuine smile on his face. "Alright, alright. I'll go be an ass somewhere else."

About an hour later, dinner was done. Everyone who wasn't lured in by the smell were called to the table. Mason smiled, seeing everyone enjoy his food, even Red who was already asking for seconds. A few took three helpings and there was still plenty left over for lunch  
Boss stood up and gave Mason a pat on the back, then leaned over a whispered into his ear. "Dinner was lovely, thank you." Boss straightened up and spoke to the room. "I shall be retiring to my room. Be sure to thank Mason for the meal and help clean up." And with that he was off.

Mason was at the sink, rinsing off dishes that each monster brought to him. Everyone of them thanked him and a few asked for the recipe. Mason was kind and had a few help him load rinsed plates into the washer. A small grouping of monsters sat around the counter chatting to each other as they munched on some of the pie that Mason had made for dessert. One monster directed himself towards the human.

"Boss has really taken a liking to you, ya know?"

Another spoke up, "Yeah, he's normally not to fond of humans. You must be something special."

"What do you think of him?"

Mason blushed and looked away, he hadn't really thought about his feelings towards Boss. He was strong, commanding, even intimidating when he needs to be. Mason remembered earlier in the evening, the small blush that the skeleton had when he questioned about the clothing choices. "Well, for a skeleton, he's pretty cute. If he were looking for some kind of romantic relationship with one of these things," Mason gestured to himself, "I definitely wouldn't say no."

"Well, we have a bet goin' now. If you guys manage together, I get to move into one of the nicer rooms close to the boss man. If ya soulbond I get the keys to one of Boss's cars."

"And Boss is okay with this?"

"He usually doesn't care about our stupid little bets. A lot of it is just swapping rooms anyways."

Mason thought he would have to ask Boss about this whole soul bonding thing later. He cut a slice of pie for himself and one for Boss before bringing them upstairs. He knocked on Bosses door and waited for a response. 

"Come in," Boss was sitting at his computer, several papers were scattered on the desk, "Oh hello Mason." He pulled off the small framed glasses he was wearing and turned around.

"You left before dessert was ready." Mason offered the slice. "It's chocolate eggy pie. It's a recipe from my grandmother."

Boss took it with a smile and led Mason over to a couch in front of the bed. He picked up the tv remote and turned it onto MTT TV, a monster channel hosted by, what some say, the world's most deadly robot. However the show itself was good and reminded Mason of one of those late night channels that had segments running from skits to game shows to interviews. It was time for the interview portion of the show, Mettaton sat behind a table and introduced his guest. 

"She's tough, she has the sharpest spears around, she's working hard to keep our streets safe, it's Undyne!"

A fish monster, clad in a police uniform, entered the frame and took a seat. "So nice to be here. But make it snappy. I got places to be."

Mettaton straightened a few cards in his hands, "I couldn't have said it better darling. Let's start with our first concern, a lot of our viewers live in a area with a lot of gang violence. What is your force doing to help?"

"We are starting to crack down on it!" Undyne sat up and made a punching motion to the camera. "My force are keeping their eyes peeled for monsters and humans alike that are contributing to heinous crimes."

Boss scoffed at the woman. "Yeah, sure." He turned to explain. "Undyne is a good friend of mine, even back in the underground. I was part of the royal guard that she headed.” He boasted, “So no need to worry about me getting caught." 

\---  
Mason was laying with Boss in the bed. He was on his phone playing a game while Boss was reading a thick book, he seemed to be about halfway through. Mason was about to ask about it when the skeleton suddenly bolted out of bed and started heading downstairs, he quickly followed behind.

"Sans, finally! Do you have any idea what time it is!?" He practically shouted at the shorter skeleton as he crossed his arms.

"i don't know, time for me to get a watch?" Red chucked at his own joke.

"The bar closed half an hour ago, where the hell were you?"

"i was just helpin' a drunken broad get home, poor thing could barely stand." Red took a long drag of the cigar that Mason had barely noticed he was holding. He tapped the ashes into a tray sitting on the end table.

Boss groaned, “Fine, but would it kill you to text me?”

“yes.”

Boss groaned again, “Just be sure to put that death stick and to dump the ashtray before you-- Great, he’s already out.” He plucked the cigar from Red’s fingers and stamped it out in the tray. He then took Mason’s hand. “Let’s get some sleep.”

**Author's Note:**

> Thank you so much for reading! 
> 
> [Please check out my fiance's chapter if you want to see what Red was up to after dinner!](https://archiveofourown.org/works/16250855/chapters/37994615)  
> Also leave a comment if you wish! It helps keep me motivated. Also please let me know if you have a better idea for the title!  
> If you would like to share fanart, please tag @shadysans on tumblr!


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